Development of Stable Carbanionic Substituents

Abstract

AbstractDuring the past decade, carbon (C−H) acids depicted as ‘Tf2CHR’ (Tf=CF3SO2) have attracted considerable attention as a new class of superacidic molecules, which show stronger acidity than sulfuric acid molecules. In recent years, the author has developed a synthetic methodology for such strong acids and has opened the door to chemistry of highly stabilised carbanions [Tf2CR]−, which are the conjugate bases of the carbon acids. These carbanion‐containing salts are stable and easy‐to‐handle species. Our efforts have revealed that the ionic but lipophilic characters of this type of carbanion can be used as a unique ‘substituent’ for increasing both the water solubility and the lipophilicity of organic compounds. This Personal Account provides an overview of our [Tf2CR]− chemistry, including its synthesis, structure, reactivity, and applications.